Methyl iodide → ethyl 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylate

HRID 2046017Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[C:9]([CH:12]3[CH2:14][CH:13]3[C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.CCOCC>[CH3:20][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[CH:12]1[CH2:14][CH:13]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 2-(4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylate (1025 mg, 4 mmol) in DMF (5 mL) was added potassium carbonate (608 mg, 4.40 mmol) followed by iodomethane (0.275 mL, 4.40 mmol) at rt. The reaction mixture was heated at 50° C. for 12 h. Cooled and diluted with ether (30 mL) and washed with water, brine and dried (Na2SO4). TLC (25% EtOAc in hexane) showed presence of starting material (10-20%). Purified by flash chromatography using 25% EtOAc in hexane to give pure ethyl 2-(1-methyl-4-phenyl-1H-imidazol-2-yl)cyclopropanecarboxylate (746 mg, 2.62 mmol, 65.5% yield). The ester solidified to a white solid over a period of time. 1H NMR (500 MHz, CHLOROFORM-d) δ 7.79-7.61 (m, 2H), 7.43-7.27 (m, 2H), 7.24-7.14 (m, 1H), 7.02 (s, 1H), 4.20 (q, J=7.2 Hz, 2H), 3.61 (s, 3H), 2.42 (ddd, J=9.0, 6.2, 4.0 Hz, 1H), 2.29 (ddd, J=8.5, 5.3, 4.1 Hz, 1H), 1.69 (ddd, J=8.5, 6.1, 4.0 Hz, 1H), 1.59 (ddd, J=9.1, 5.3, 3.9 Hz, 1H), 1.30 (t, J=7.1 Hz, 3H); MS (ESI) 271 (M+H); Rf=1.90 (Condition A).

Workup

temperatureCooled
washwashed with water, brine
dry with materialdried (Na2SO4)
customPurified by flash chromatography

Sources & evidence

ORD record: ord-c203f3c61a9f422a9f4eeabee8f2f5bd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592423B2

Reaction notes

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